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6285 Shady, Shady Side
$695,000
4 Beds ⋅ 3 Baths
Endless potential in this versatile property — live in one side and run your business from the other, or use the entire building for commercial use. Originally the Shady Side Post Office, this character-filled building sits on just over half an acre with approximately 400 feet of road frontage, offering excellent visibility and easy access Highlights: C1 commercial zoning — flexible uses Live/work configuration or full commercial conversion Multiple offices / bedrooms 3 Bath rooms 2 kitchens and 2 laundry areas Just over 0.5 acre lot with 400' road frontage Suitable for: accountant, attorney, construction office, daycare, antiques, boat sales/service, retail, studio, café, professional offices, and more Why this property: Great exposure and versatility make this an ideal opportunity for owner-operators or investors looking to attract customers and create a distinctive business presence. High frontage and flexible zoning mean almost any business concept could work here.

6285 Shady, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4922 Lerch Dr, Shady Side
$699,000
3 Beds ⋅ 3 Baths
You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stunning, open concept, 3-bedroom, 3-bath home was built in 2005 and has a PRIVATE dock -- blending modern updates, natural light, and serene water views. This home is the ideal size—not too big, not too small—offering the perfect balance of comfort, function, and privacy! Step inside an inviting open-concept main level to find luxury plank flooring throughout, and a cozy fireplace that anchors the living space. The chef’s kitchen is a showstopper, featuring a spacious island, sleek countertops, white cabinetry, and stainless appliances—ideal for entertaining and everyday living. The main level also offers a bedroom and full bath! The upper level boasts a dreamy primary suite overlooking the water, bathed in sunlight and featuring new, expansive windows . Enjoy the expansive STUNNING walk-in closet and spa-like en-suite bath with dual vanity, soaking tub, wainscoting, and a beautifully tiled frameless glass shower. Two additional bedrooms (one on main level) and bathrooms provide comfort , style and functionality with plenty of room for everyone! Outdoor living is just as special—this quiet retreat features a private dock, a fenced backyard, a paver patio and plenty of storage. Picture mornings with coffee and sunrise views, evenings on the patio watching the sunset reflect across the water, or weekends spent crabbing, kayaking, fishing, boating right from your own backyard! Not to forget a new roof (2024)! Situated in Shady Side, you’ll love the easy access to the Bay & only 25 minutes to Annapolis, 40 minutes to Washington, D.C., and 45 minutes to Northern Virginia. This home offers the perfect balance of waterfront tranquility and city convenience. So many local marinas, restaurants & the Chesapeake Yacht Club is nearby with memberships and slips available! Don’t miss this rare opportunity to occupy a turn-key waterfront property at this price point!

4922 Lerch Dr, Shady Side

Listing courtesy of Samson Properties. Contact:

1240 Hawthorne St, Shady Side
$464,999
3 Beds ⋅ 3 Baths
REDUCED ALMOST 25K >>> HURRY THIS PROPERTY WILL NOT LAST LONG AT THIS PRICE>>>>.Nestled in the charming Avalon Shores community, this delightful Colonial home offers a perfect blend of comfort and modern living. This 3 bedroom and 2.5 bath has a thoughtfully designed space, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with beautiful LVT floors. The huge eat-in kitchen with under cabinet lighting and stainless appliances is great for a family & entertaining with a huge dining area off kitchen. The spacious primary suite offers a serene retreat with new LVT floors and a newly remodeled bath with new vanity, new LVT floors, lighting and toilet. The separate laundry room upstairs is and added bonus!! Outside the extensive hardscape with new concrete walkways complements the lovely 17 x17 back patio and 28x10 back deck and front porch all perfect for enjoying morning coffee or evening gatherings with family and friends. The level lot with maintenance free fenced in yard provides a lovely outdoor space, while the attached garage and asphalt driveway ensure ample parking. The home is wired with a full subpanel for in house generator. There is an encapsulated crawlspace with Aquaguard w/ EZ Breath climate control and dehumidifier. Residents of Avalon Shores enjoy exclusive access to common grounds and picnic areas, a pier/dock, and playground, fostering a sense of community and outdoor enjoyment. With water and lake privileges, you can embrace a lifestyle filled with leisure and recreation. This home is not just a property; it's a sanctuary where family memories are made. Experience the perfect blend of comfort, convenience, and community in this exceptional family oriented home.

1240 Hawthorne St, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

1241 Johnson Dr, Shady Side
$680,000
3 Beds ⋅ 3 Baths
***OPEN HOUSE*** Sun 11/8 11am-1pm. Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! Welcome to your own private waterfront retreat nestled at the peaceful head of South Creek, where breathtaking views, abundant wildlife, and the ultimate Chesapeake Bay lifestyle come together. Perfectly positioned on a beautifully level lot, this exceptional property offers a private pier ideal for launching a kayak, canoe, paddleboard, or boat, while the nearby community marina provides access to deep-water slips for larger vessels. Residents also enjoy access to the community beach, making every day feel like a vacation. An added bonus is the inclusion of the adjacent Lots 17 & 18 (4907 Thomas Drive), providing additional privacy, flexibility, and future possibilities. Step inside to discover a bright, open floor plan designed to maximize both the water views and natural light. The spacious kitchen features a center island, ample cabinetry, and a sunny breakfast area highlighted by a large picture window overlooking the creek—an unforgettable place to enjoy your morning coffee. The adjoining living room offers the warmth and charm of a wood-burning stove along with sliding glass doors leading to the expansive wraparound screened porch, creating the perfect space for indoor-outdoor entertaining or simply relaxing while watching osprey, herons, and other local wildlife. Large pantry area for additional storage and separate dining room for additional room to spread out. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite that serves as a true waterfront sanctuary. Wake up each morning to panoramic water views from your private balcony, then unwind in the en-suite bath featuring a walk-in closet and plenty of room to recharge after a day on the water. The additional bedrooms are generously sized, with one also enjoying beautiful water views, and are served by a second full bathroom on the upper level. This home has been thoughtfully updated for peace of mind and long-term enjoyment. It may say it was built in 1941, but this home went through an extensive remodel in 1991 taking the original beach bungalow to the oversized colonial it is today. Recent improvements include a brand-new roof (2026), renovated Tigerwood deck, and a professionally encapsulated crawlspace complete with a dehumidification system. If you’ve been dreaming of a waterfront lifestyle that combines privacy, natural beauty, and everyday comfort, this is a rare opportunity to own a special piece of Southern Anne Arundel County. Whether you’re boating, crabbing, kayaking, entertaining on the screened porch, or simply enjoying the peaceful creek views, you’ll quickly understand why this location is so special.

1241 Johnson Dr, Shady Side

Listing courtesy of RE/MAX One. Contact:

4951 Bonniewood Dr, Shady Side
$470,000
3 Beds ⋅ 3 Baths
Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered for sale by only its original builders of the home. Situated on over one-third of an acre, this well-maintained 3-bedroom, 2.5-bath residence offers the perfect blend of comfort, space, and community living. The fully fenced backyard provides an ideal setting for entertaining, family gatherings, or simply relaxing outdoors. Inside, the updated kitchen features granite countertops and stainless steel appliances, while gorgeous hardwood floors with custom inlay accents add warmth and character throughout the home. The spacious primary suite boasts vaulted ceilings and a private en-suite bath, creating a comfortable retreat. All bedrooms are generously sized and offer ample closet space. Enjoy peaceful mornings with a cup of coffee or unwind in the evenings on the charming enclosed front porch, perfect for reading or taking in the neighborhood atmosphere. Residents of Avalon Shores enjoy exceptional community amenities, including two playgrounds, baseball fields, a community boat launch, and water access. Opportunities like this are rare in such a desirable waterfront community. Don't miss your chance to make this wonderful home your own!

4951 Bonniewood Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

4950 Bonniewood Dr, Shady Side
$765,000
3 Beds ⋅ 2 Baths
Waterfront living with a private dock—all for only $765,000! Get a lower mortgage payment! Seller willing to supplement rate discount, 2-1 Buydown: 2% lower interest rate in Year 1, and 1% lower in Year 2. Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious fully-fenced backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage with a 12kW Level 2 EV charger, offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

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